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Nantucket: The Far Away Land

Writer Herman Melville once called it “an elbow of sand” and the native Wampanoag Indians named it “the Faraway land” (or Nantucket). Both names fit this 14-mile-long and 3.5-mile-wide island 30 miles off the Massachusetts coast. A recent addition to the island’s genteel way of life is the family-friendly Westmoor Club and its flagship Belle.
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Writer Herman Melville once called it “an elbow of sand” and the native Wampanoag Indians named it “the Faraway land” (or Nantucket). Both names fit this 14-mile-long and 3.5-mile-wide island 30 miles off the Massachusetts coast. A recent addition to the island’s genteel way of life is the family-friendly Westmoor Club and its flagship Belle.

From the mid-1700s to 1840, Nantucket was a thriving whaling seaport, a heritage that the islanders have proudly preserved in museums and exhibits. These days, Nantucket is equally well known as a prime sailing destination for regattas. During the summer season, more than 3,000 boats navigate this remote island’s shoals, known in some circles by the moniker “The Grey Lady” because it is regularly shrouded in fog. The rollicking Figawi Race in late May, which kicks off the sailing season in New England, was named after the frequently heard lament, “Where the….are we?” as racers often have to compete in dense fog. But, come August, Nantucket redeems herself for the popular Opera House Cup sailing race, often held under a brilliant blue sky, combined with strong winds and choppy seas—in short, a sailor’s delight. But it is the architecture, commitment to preservation, and its charm and authenticity that make Nantucket such a magnet for tourism, essential to maintaining the quality of life on this treasured island, a designated National Historic landmark. The few blocks that comprise the downtown and harbor remain much as they were in the 1700s. The oldest house, the Jethro Coffin House, dates back to 1686, among more than 800 pre-Civil War buildings. The town is still made up of meandering cobblestone streets, pathways of broken shells, gas streetlights and gray-shingle wharf shacks, home now to boutiques and restaurants, alongside glorious houses built by wealthy former sea captains. Visitors often feel like they are stepping back in time, but don’t be fooled by the farmland, cranberry bogs and craggy moors, Nantucket has always catered to the upscale tourist. The island is a combination of sophistication and luxury with an air of genteel and proper manners. It appeals to an intense, accomplished group of summer travelers. Despite the island’s natural beauty, to live here the locals have to endure sacrifice, so they tend to be intense characters as well, which makes for a great mix. Though a land-conservation trust protects more than a third of the island from development, right outside of town, sprawling houses dot the landscape and locals take umbrage at the number of four-wheel-drive Range Rovers navigating their way through town’s narrow streets. Still, civility prevails. Accommodations can be scarce and tend to be pricey. Lodgings such as the The Wauwinet, a Relais & Châteaux, the White Elephant and the Cliffside Beach Club are all luxury properties, but their Nantucket style means that they are more intimate in scale. For fine dining, expect New York prices. Diners will savor every bite, though, as skillful chefs such as Todd English do honor to the local produce, meats, Nantucket Bay scallops and lobsters plucked moments before, fresh from the sea.


Don’t even consider making this a day trip; it takes a few days to get into the island’s rhythm. Unless you are traveling the waterways in your own pleasure craft, you can fly over on a puddle jumper. When arriving by air, in an hour or less in many cases, visitors can be twinkling heir toes on the sandy beaches along the 80 miles of coastline stretching from the calm waters of Nantucket Sound to the pounding surf of the Atlantic Ocean. Fishermen delight in the island. Cast for bluefish in the shallow water, tackle white water for striped bass or venture farther out to sea for tuna and shark. And local clubs offer everything from boat outings to tennis courts and rounds of golf.

A landscape of the Westmoor Club by local artist Ilya Kagan

A landscape of the Westmoor Club by local artist Ilya Kagan

The Westmoor Club, which opened in 2005, is the newest addition to the Nantucket country-club scene. With the legacy programs completely full at the Nantucket Yacht Club and the Sankaty Head Golf Club, there was a need for a newcomer to offer a meeting place for family and friends. The aim is to offer members 19th-century grace and elegance and 21st-century comfort and convenience. The 15-acre property, just 300 yards from Nantucket Sound, was once part of the Vanderbilt estate, and the club’s designers have retained the integrity of the 1917 Colonial Revival mansion. The interior boasts a spacious-but-elegant dining room and cozy wood-paneled bar where members and guests can relax after a round of sports on the 10 Har-Tru tennis courts, three grass tennis courts, croquet field, two squash courts, children and adults’ swimming pools, and a newly constructed 18,000-square-foot spa and fitness center. With raw-cut pine boards, exposed beams and a great room with fireplace, the building fits in well with the club’s historic architecture. Children three to 12 can attend the sport camps, while parents can enjoy some quiet moments by the pool with a healthy lunch washed down with the specialty wheat-grass smoothie from the on-site vegetable and herb garden. A few rooms are available for overnight stays, invaluable in a town where accommodations are hard to get.

This would not be Nantucket without a nautical component. While children participate in the community sailing program, club members have access during Nantucket Race Week to one of the oldest remaining 12-Metre sailboats, Onawa, or a crewed sportfishing boat available for charters and club-sponsored excursions. For harbor tours, dinner trips, lunch outings and prime viewing for yacht races, many guests request the classic 77-foot Belle. The New York Yacht, Launch and Engine Company built the yacht in 1929 using Douglas fir planking on steam-bent white-oak frames.

Scott Oliver enjoys his role as Belle’s captain. “The boat is all original. She has cable steering, a single rudder, no joystick here. She has a plumb bow and a really narrow beam, so she just cuts through the water. In any kind of head sea or falling sea, she’s great, a pleasure to drive.” The maintenance is constant, but he takes it in stride. “It really is a labor of love, keeping up all the varnish work. Belle has a teak deck, mahogany superstructure and white oak framing. She’s like a living entity, and you have to keep her in the water to keep her alive,” he says. “Classic wooden boats may not be for everyone. Many of the traditions of the golden age of yachting are falling by the wayside; people don’t even raise the flag at 8 am and pull it down at sunset anymore, but for me it’s important to keep the traditions alive. Belle is a real head-turner. I hate to be a boat snob, but it’s nice to be on a pretty boat!”


The popular aft deck has a large settee, and though the boat typically is used just for day sails or cocktails for up to 40 people, she can accommodate an overnight trip for eight. Oliver remembers a recent birthday party for an elderly family member. Lanterns decorated the boat and guests enjoyed a candlelit lobster dinner. Once the meal was complete, guests turned their chairs around and traded stories about the honored grandfather. A musician played the ukulele in the background as the harbor lights cast a glow on the water. “It’s a good boat for families, to be able to just cast a line and slip away for a while.” Now a permanent part of The Westmoor Club fleet, Belle is one of 35 or so classic yachts offered through the Vintage Yachting Club. VYC offers seasonal and annual yachting programs for members and will occasionally charter to non-members. Some of the yachts available include a 27-foot Herreshoff S-boat, perfect for sailing; the 75-foot Trumpy America, and the 80-foot schooner Lelanta. Aside from a one-time $5,000 fee, annual membership fees range from $1,500 (for the entry-level membership) to more than $100,000, the higher range ideal for corporations looking to provide the ultimate experience. “VYC offers a growing portfolio of lifestyle experiences and yacht-charter offerings including access to global excursion events and amenities from our network of luxury partners, such as Small Luxury Hotels of the World,” says President Eric Dahler. Some of the upcoming events this season for members to partake in include a Newport excursion weekend for the America’s Cup World Series in July, complete with hospitality yacht for members and guests, spectator boats to view the race, cocktail receptions and a resort-wear fashion show.

So think about experiencing Nantucket, at least once. Toss one of those Nantucket faded red caps on your head, rent a simple bicycle to tool around town, stop by for a Dark ’n’ Stormy to meet some of the locals at The Club Car piano bar, a former train club car with a narrow interior that encourages friendly banter and, for dinner, walk over to the global bistro Lola 41, another local favorite. Find the time to visit Siasconset, better known as “Sconset,” where rose bushes weave their way between white picket fences surrounding restored fishing shacks. If traveling by boat, just as you round the lighthouse at Brant Point, follow tradition and toss a penny overboard, in hopes that you’ll return some day, joining the many “washashores” that now call Nantucket home. ■

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To see our Insiders Guide to Nantucket, click here. To view this article in our digital magazine, click here.